Pyridine → 2,8-Dimethyl-3H-quinazolin-4-one

HRID 429168Notes

Reaction equation

HRID 429168 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=[CH:14][CH:13]=1.C(Cl)(=O)C>C1COCC1>[CH3:13][C:14]1[NH:6][C:4](=[O:5])[C:3]2[C:2](=[C:10]([CH3:11])[CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 142218072-Amino-3-methylbenzamide

Product 1

HCID 1354635742,8-Dimethyl-3H-quinazolin-4-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-3-methylbenzamide (0.5 g, 3.3 mmol) (prepared by conventional methods) and pyridine (0.35 ml, 4.3 mmol) in dry THF (15 ml), was added a solution of acetyl chloride (0.36 ml, 5.0 mmol) in THF (2 ml). dropwise, and the mixture was stirred overnight under nitrogen. The solvent was removed under vacuum and the remaining white slurry was resuspended in 2% aqueous sodium hydroxide solution and neutralised with aqueous hydrochloric acid, whereupon a white precipitate formed. The solid was collected and recrystallised from methanol-water to furnish the required quinazolinone (0.47 g, 81%) m.p. 217-220° C.;

Workup

  1. customThe solvent was removed under vacuum
  2. customformed
  3. customThe solid was collected
  4. customrecrystallised from methanol-water

Sources & evidence

ORD record
ord-d640e9aa81384142aadfe73442f9d63e
Source dataset
uspto-grants-2001_11
Patent number
US06316455B1

Reaction notes

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